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Three-component condensation of Meldrum’s acid with 2-naphthylamine and esters derived from vanillin

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Abstract

Three-component condensation of Meldrum’s acid (2,2-dimethyl-1,3-dioxane-4,6-dione) with 2-naphthylamine and esters derived from vanillin involves intermediate formation of N-arylmethylidene-2-naphthylamines which are cleaved with Meldrum’s acid to give 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones and arylmethylideneketenes. Reaction of the latter with 2-naphthylamine leads to formation of 2-methoxy-4-(3-oxo-1,2,3,4-tetrahydrobenzo[f]quinolin-1-yl)phenyl carboxylates.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    N. G. Kozlov & L. I. Basalaeva

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  1. N. G. Kozlov
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  2. L. I. Basalaeva
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Original Russian Text © N.G. Kozlov, L.I. Basalaeva, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 4, pp. 527–532.

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Kozlov, N.G., Basalaeva, L.I. Three-component condensation of Meldrum’s acid with 2-naphthylamine and esters derived from vanillin. Russ J Org Chem 42, 509–514 (2006). https://doi.org/10.1134/S1070428006040063

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  • DOI: https://doi.org/10.1134/S1070428006040063

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